Alan Jones, the pyjamas and the ponies

Alan Jones’ long-term racing partner John Leaver was in his pyjamas when the Australian Federal Police raided his Point Piper mansion late one evening in October 2013.

Mr Leaver’s arrest attire only came to light when the prominent broadcaster gave the Australian Tax Office both barrels on his radio program the following morning.

Jones’ spray against the ATO following his racing partner’s arrest is just one of a number of occasions where he has used his radio program to attack - or praise - interests associated with thoroughbreds. Rarely does he disclose his substantial financial interests in the thoroughbred industry, worth between $20 million and $40 million, according to industry insiders.

Industry insiders suggest Alan Jones' financial interests in the thoroughbred industry are worth between $20 million and $40 million. Credit:AAP

On Tuesday, a fulminating Jones said people had accused him of "[saying] what I said [because] I live at the Toaster, and I own racehorses. That was my motivation. I think you're reaching to the bottom of the birdcage if that's the best you can do." A short time later he gave a grudging apology to Ms Herron.

Jones did not have a horse starting in what has been billed as the world’s richest turf race, The Everest, but his racing partner John Messara owns Shoals.

More significantly, the fact that Redzel won and Trapeze Artist came second in Saturday's $13 million race could lead to a major windfall for Jones and his racing partners Mr Leaver and Mr Messara.

Kerrin McEvoy rides Redzel to victory in The Everest at Royal Randwick. Credit:AAP

The trio is part of a syndicate which owns sire champion stallion Snitzel, which stands at Mr Messara's Arrowfield Stud in the Hunter Valley.

With Redzel's prize winnings now more than $15 million and Trapeze Artist at $5.2 million, both the stud fees (and value) of their sire Snitzel are set to increase.

Snitzel had the potential earnings of $44 million this year as he "covered" an estimated 200 mares at $220,000 a pop. However, corporate records show that there are 40 shares in the Snitzel syndicate and each share entitles the owner to a free service from Snitzel. In some cases, the Snitzel syndicate can waive the service fee for a mare in return for a 50 per cent share from the sale of the resulting progeny.

Jones, who has a 6.25 per cent share in Snitzel, received almost $400,000 in after-tax profits from that one horse last financial year.

Snitzel is just one of the dozens of horses Jones has an interest in. For instance, last year a colt from two horses in which Jones has an interest - stallion Dundeel and champion mare Miss Finland - sold for $900,000 at the Magic Millions yearling sale.

From left to right: trainer David Hayes celebrates Miss Finland's 2006 Crown Oaks win with her owners John Leaver, John Messara and Alan Jones.Credit:Sebastian Costanzo

Ms Herron was not the first to be on the receiving end of a Jones tirade about perceived failures to boost the racing industry. On the eve of the 2015 state election, he tore into then-premier Mike Baird for not publicly committing to a better deal for racing. Liberal sources have claimed that the bruising interview left Mr Baird privately fuming.

Legendary turf reporter Ken Callander was the subject of an extraordinary invective when he did not support Mr Messara’s appointment to the Racing NSW board.

Ken Callander. Credit:AAP

"The dissidents have for months found a mouthpiece in the racing writer Ken Callander, whose performance in all of this has been absolutely appalling ... his credibility shot to pieces," fumed Jones on air in 2008.

Callander retaliated in The Daily Telegraph, writing: “At the start of his spray yesterday Jones said he was going to talk on racing. ‘Let me declare an interest,’ he said. ‘I have a bit to do with horse racing.’ That is all he said. What interest did he declare? Absolutely none.

“Alan did not tell you he is best mates with John Messara, the candidate who missed out on a position on the Racing NSW board and is a part owner with him in super stallion Redoute's Choice,” Mr Callander wrote.

Callander said that Jones’ other interest, which he failed to declare, was that he “pockets thousands” each year through his shareholding with Mr Messara in Redoute's Choice which was serving approximately 150 mares per season at $330,000 per mare.

The previous year, the estimated $50 million per annum stud fees generated by Redoute's Choice were in jeopardy during the equine flu crisis. The government-imposed lockdown meant that broodmares couldn’t travel. Jones went into full battle mode, railing against the then NSW Labor government.

"There is one bloke in Macquarie Street who has been working his butt off and doing a damn good job in difficult circumstances and this is the Primary Industries Minister – Ian Macdonald," said Jones in September 2007.

"I think you should be running the trains, the desalination plant and everything," he said of the now-jailed Macdonald.

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But later that same year, Mr Messara’s efforts in organising airline upgrades to thank Macdonald for lifting the broodmare travel ban, which saved Mr Messara and other Hunter Valley breeders millions in dollars, effectively ended the controversial minister’s career.

Caught lying about the upgrades, Macdonald was sacked from the cabinet and he left State Parliament soon after.

Over the years, Jones has owned over a hundred racehorses. His fellow owners have included swimmer Grant Hackett and an array of cricketing figures including Shane Watson and Brett Lee. He currently races a filly Never Out - which has won $110,000 - with cricketers Aaron Finch, Glenn Maxwell, Andrea Lehmann (wife of former national coach Darren), and brothers Shaun and Mitch Marsh.

Relaunch, a horse he raced with real estate supremo John McGrath, never made it further than barrier trials. While Manifest, Trusted and Who’s Inside, which he co-owned with James Packer, enjoyed moderate successes.

Sydney Opera House CEO Louise Herron.Credit:Jessica Hromas

But his biggest successes, including with Miss Finland, have come via his long-running racing partnership which consists of Jones, through his company Belford Productions, Mr Messara, through Arrowfield Pastoral, and John Leaver, through Planette Thoroughbred Trading.

The criminal charges for money laundering and tax evasion levelled against Mr Leaver and Vanda Gould, then co-owner of the pair’s racing syndicate Planette Thoroughbred, were later dropped. However, a later court civil case found that $7.8 million was transferred to Mr Gould and Mr Leaver’s racing company via a series of companies in overseas tax havens.

In late 2015, Mr Leaver quietly agreed to pay $25.87 million in taxes and penalties to the ATO.

Mr Gould was also hit with multimillion-dollar tax penalties, and a fresh trial date is yet tobe set for a charge of attempting to pervert the course of justice, stemming from his fight withthe ATO.